Synthesis of (±)-Nosyberkol (Isotuberculosinol, Revised Structure of Edaxadiene) and (±)-Tuberculosinol

Abstract

Me(2)AlCl-catalyzed Diels-Alder reaction of N-tigloyloxazolidinone with 6,6-dimethyl-1-vinylcyclohexene selectively provided the exo adduct, which was converted to nosyberkol (isotuberculosinol) and tuberculosinol. The spectral data for nosyberkol are identical with those reported for edaxadiene, whose structure is revised accordingly.